CZ291124B6 - Derivát N-arylthiohydrazonu, způsob jeho přípravy, způsob a prostředek pro hubení hmyzích a roztočových ąkůdců a způsob ochrany rostlin před těmito ąkůdci - Google Patents

Derivát N-arylthiohydrazonu, způsob jeho přípravy, způsob a prostředek pro hubení hmyzích a roztočových ąkůdců a způsob ochrany rostlin před těmito ąkůdci Download PDF

Info

Publication number: CZ291124B6
Authority: CZ; Czechia
Prior art keywords: optionally substituted; halogen; alkyl; alkoxy; haloalkoxy
Prior art date: 1994-10-27

Application number

CZ19952743A

Other languages

Czech (cs)

English (en)

Other versions

CZ274395A3 (en

Inventor

Susan Trotto

Joseph Augustus Furch

David George Kuhn

David Allen Hunt

Original Assignee

American Cyanamid Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-10-27

Filing date

1995-10-20

Publication date

2002-12-11

1995-10-20 Application filed by American Cyanamid Company filed Critical American Cyanamid Company

1996-05-15 Publication of CZ274395A3 publication Critical patent/CZ274395A3/cs

2002-12-11 Publication of CZ291124B6 publication Critical patent/CZ291124B6/cs

Links

238000000034 method Methods 0.000 title claims abstract description 32
239000000203 mixture Substances 0.000 title claims abstract description 23
241000607479 Yersinia pestis Species 0.000 title claims abstract description 18
241000238631 Hexapoda Species 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical group 0.000 claims description 57
125000005843 halogen group Chemical group 0.000 claims description 38
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
125000004093 cyano group Chemical group *C#N 0.000 claims description 36
125000001424 substituent group Chemical group 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 27
-1 at least one of A Inorganic materials 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 25
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000002689 soil Substances 0.000 claims description 7
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
208000015181 infectious disease Diseases 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000013543 active substance Substances 0.000 abstract 1
125000006414 CCl Chemical group ClC* 0.000 description 69
150000001875 compounds Chemical class 0.000 description 41
241000196324 Embryophyta Species 0.000 description 19
238000012360 testing method Methods 0.000 description 16
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
238000000921 elemental analysis Methods 0.000 description 9
230000000749 insecticidal effect Effects 0.000 description 9
206010061217 Infestation Diseases 0.000 description 8
230000000895 acaricidal effect Effects 0.000 description 8
238000011156 evaluation Methods 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
238000010183 spectrum analysis Methods 0.000 description 7
241000238876 Acari Species 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000003517 fume Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
150000007857 hydrazones Chemical class 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
101150065749 Churc1 gene Proteins 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000256257 Heliothis Species 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
102100038239 Protein Churchill Human genes 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
239000012895 dilution Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
239000003480 eluent Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
230000009931 harmful effect Effects 0.000 description 2
239000000123 paper Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
MHGMECVOEBGLAX-UHFFFAOYSA-N s-ethyl 2,2-dimethylpropanethioate Chemical compound CCSC(=O)C(C)(C)C MHGMECVOEBGLAX-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
UTAYPBUZQVZJMU-UHFFFAOYSA-N 2,2-dimethyl-N'-(2,4,6-trichlorophenyl)propanehydrazide Chemical compound CC(C)(C)C(=O)NNC1=C(Cl)C=C(Cl)C=C1Cl UTAYPBUZQVZJMU-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
STABAPSYCQFWOK-UHFFFAOYSA-N 4-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C(Cl)C=C1 STABAPSYCQFWOK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
241000239290 Araneae Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
125000005865 C2-C10alkynyl group Chemical group 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000995023 Empoasca Species 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
241000256244 Heliothis virescens Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
244000211187 Lepidium sativum Species 0.000 description 1
235000007849 Lepidium sativum Nutrition 0.000 description 1
241000819999 Nymphes Species 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
244000062793 Sorghum vulgare Species 0.000 description 1
241001521235 Spodoptera eridania Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009418 agronomic effect Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000003124 biologic agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000011284 combination treatment Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
238000011161 development Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical class OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000004530 micro-emulsion Substances 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CZ19952743A 1994-10-27 1995-10-20 Derivát N-arylthiohydrazonu, způsob jeho přípravy, způsob a prostředek pro hubení hmyzích a roztočových ąkůdců a způsob ochrany rostlin před těmito ąkůdci CZ291124B6 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/330,047 US5556885A (en)	1994-10-27	1994-10-27	N-aryl- and N-heteroarylhydrazones of substituted thioacids and the s-oxides thereof as insecticidal and acaricidal agents

Publications (2)

Publication Number	Publication Date
CZ274395A3 CZ274395A3 (en)	1996-05-15
CZ291124B6 true CZ291124B6 (cs)	2002-12-11

Family

ID=23288089

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ19952743A CZ291124B6 (cs)	1994-10-27	1995-10-20	Derivát N-arylthiohydrazonu, způsob jeho přípravy, způsob a prostředek pro hubení hmyzích a roztočových ąkůdců a způsob ochrany rostlin před těmito ąkůdci

Country Status (20)

Country	Link
US (1)	US5556885A (da)
EP (1)	EP0709372B1 (da)
JP (1)	JP3902677B2 (da)
KR (1)	KR100408378B1 (da)
CN (1)	CN1081185C (da)
AT (1)	ATE170172T1 (da)
AU (1)	AU705481B2 (da)
BR (1)	BR9504570A (da)
CA (1)	CA2161375A1 (da)
CZ (1)	CZ291124B6 (da)
DE (1)	DE69504272T2 (da)
DK (1)	DK0709372T3 (da)
ES (1)	ES2122460T3 (da)
GR (1)	GR3027763T3 (da)
HU (1)	HU219147B (da)
IL (1)	IL115769A (da)
SI (1)	SI0709372T1 (da)
SK (1)	SK282788B6 (da)
TW (1)	TW366259B (da)
ZA (1)	ZA959122B (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2000514815A (ja)	1996-07-24	2000-11-07	ノバルティスアクチェンゲゼルシャフト	農薬組成物
US6242647B1 (en)	1998-12-03	2001-06-05	American Cyanamid Company	Insecticidal biphenylthiohydrazides
WO2002098841A1 (en) *	2001-06-05	2002-12-12	Basf Aktiengesellschaft	Insecticidal biphenylthiohydrazides
CN1199939C (zh) *	2002-09-13	2005-05-04	湖南化工研究院	具有杀虫、杀菌、除草活性的含烷硫烷基腙类衍生物及其制备方法
DE102004031323A1 (de) *	2004-06-29	2006-01-19	Bayer Cropscience Ag	Substituierte Pyridazincarboxamide und Derivate hiervon
BRPI0619187A2 (pt) *	2005-12-01	2011-09-13	Sumitomo Chemical Co	composto de iminopropeno e uso do mesmo
JP5239148B2 (ja) *	2005-12-01	2013-07-17	住友化学株式会社	３−イミノプロペン化合物、それを含有する有害生物防除剤、およびその有害生物防除用途
CN119977855B (zh) *	2025-04-15	2025-07-08	山东金科力电源科技有限公司	一种硫代腙类化合物的合成方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3332936A (en) *	1962-09-28	1967-07-25	Du Pont	Bis(phenylsulfonyl)diazomethanes and their preparation
GB1090146A (en) *	1965-06-17	1967-11-08	Shell Int Research	Dichlorothiobenzoylhydrazines and their use as herbicides
US3423409A (en) *	1965-11-01	1969-01-21	Ciba Geigy Corp	Triazines
US3829492A (en) *	1972-02-04	1974-08-13	Rohm & Haas	Fungicidal salicylaldehyde hydrazones and azines
US3867449A (en) *	1974-05-16	1975-02-18	Chevron Res	Insecticidal phenylhydrazone sulfides
JPS5564557A (en) *	1978-11-08	1980-05-15	Mitsui Toatsu Chem Inc	Diphenyl ether compound and herbicide containing the same
US4621156A (en) *	1979-10-29	1986-11-04	Polaroid Corporation	Optical filter agents and photographic products and processes containing same
GB9117987D0 (en) *	1991-08-20	1991-10-09	Ici Plc	Heterocyclic compounds

1994
- 1994-10-27 US US08/330,047 patent/US5556885A/en not_active Expired - Lifetime
1995
- 1995-10-16 TW TW084110861A patent/TW366259B/zh active
- 1995-10-20 CZ CZ19952743A patent/CZ291124B6/cs not_active IP Right Cessation
- 1995-10-25 CA CA002161375A patent/CA2161375A1/en not_active Abandoned
- 1995-10-25 IL IL11576995A patent/IL115769A/xx not_active IP Right Cessation
- 1995-10-26 AT AT95307639T patent/ATE170172T1/de not_active IP Right Cessation
- 1995-10-26 EP EP95307639A patent/EP0709372B1/en not_active Expired - Lifetime
- 1995-10-26 KR KR1019950037350A patent/KR100408378B1/ko not_active Expired - Fee Related
- 1995-10-26 JP JP30045295A patent/JP3902677B2/ja not_active Expired - Fee Related
- 1995-10-26 SI SI9530078T patent/SI0709372T1/xx not_active IP Right Cessation
- 1995-10-26 DE DE69504272T patent/DE69504272T2/de not_active Expired - Lifetime
- 1995-10-26 ES ES95307639T patent/ES2122460T3/es not_active Expired - Lifetime
- 1995-10-26 CN CN95119017A patent/CN1081185C/zh not_active Expired - Fee Related
- 1995-10-26 HU HU9503070A patent/HU219147B/hu not_active IP Right Cessation
- 1995-10-26 DK DK95307639T patent/DK0709372T3/da active
- 1995-10-26 BR BR9504570A patent/BR9504570A/pt not_active IP Right Cessation
- 1995-10-27 SK SK1352-95A patent/SK282788B6/sk unknown
- 1995-10-27 AU AU34527/95A patent/AU705481B2/en not_active Ceased
- 1995-10-27 ZA ZA959122A patent/ZA959122B/xx unknown
1998
- 1998-08-27 GR GR980401942T patent/GR3027763T3/el unknown

Also Published As

Publication number	Publication date
JPH08239359A (ja)	1996-09-17
ATE170172T1 (de)	1998-09-15
JP3902677B2 (ja)	2007-04-11
CZ274395A3 (en)	1996-05-15
DE69504272D1 (de)	1998-10-01
KR100408378B1 (ko)	2004-03-02
AU3452795A (en)	1996-05-09
CA2161375A1 (en)	1996-04-28
HU219147B (hu)	2001-02-28
DE69504272T2 (de)	1999-05-27
AU705481B2 (en)	1999-05-20
EP0709372B1 (en)	1998-08-26
CN1081185C (zh)	2002-03-20
HUT73816A (en)	1996-09-30
IL115769A (en)	2000-02-17
CN1131667A (zh)	1996-09-25
US5556885A (en)	1996-09-17
IL115769A0 (en)	1996-01-19
ZA959122B (en)	1997-09-28
TW366259B (en)	1999-08-11
SK282788B6 (sk)	2002-12-03
SI0709372T1 (en)	1998-10-31
GR3027763T3 (en)	1998-11-30
ES2122460T3 (es)	1998-12-16
DK0709372T3 (da)	1998-11-09
KR960013202A (ko)	1996-05-22
SK135295A3 (en)	1996-06-05
EP0709372A1 (en)	1996-05-01
BR9504570A (pt)	1997-02-25
HU9503070D0 (en)	1995-12-28

Legal Events

Date	Code	Title	Description
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic
2006-06-14	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20051020

Publication	Publication Date	Title
KR960002556B1 (ko)	1996-02-22	이미다졸 화합물 및 이를 함유하는 유해 유기체 방제용 살균 조성물
JP2610988B2 (ja)	1997-05-14	新規ヘテロ環式化合物及び殺虫剤
JP2583429B2 (ja)	1997-02-19	イミダゾリン類及び殺虫剤
RU2092479C1 (ru)	1997-10-10	Производные 1-арилпирролов, инсектоакарицидонематоцидная композиция и способ борьбы с насекомыми
JPH0717621B2 (ja)	1995-03-01	新規ヘテロ環式化合物
JP3816543B2 (ja)	2006-08-30	殺昆虫剤および殺ダニ剤としてのｎ−アリールヒドラジン誘導体
JPH0710865B2 (ja)	1995-02-08	ニトロ置換ヘテロ環式化合物及び殺虫剤
WO1991007392A1 (en)	1991-05-30	Pesticidal pyrimidinyl benzoic acids and esters
DE69133140T2 (de)	2003-03-20	2-Aryl-5-(trifluoromethyl)-2-pyrrolinderivate und Verfahren zur Herstellung von 2-Aryl-1-(alkoxymethyl)-4-halo-5-(trifluoromethyl)-pyrrolen mit insektizider Wirkung
HUT54130A (en)	1991-01-28	Derivates of 5-alkyl-1,3,4-thiadiazole, process for producing them and their usage as nematocide
JP4763195B2 (ja)	2011-08-31	農薬としてのテトラヒドロピリジン
CZ291124B6 (cs)	2002-12-11	Derivát N-arylthiohydrazonu, způsob jeho přípravy, způsob a prostředek pro hubení hmyzích a roztočových ąkůdců a způsob ochrany rostlin před těmito ąkůdci
JPH06172348A (ja)	1994-06-21	有害生物防除剤
SK113793A3 (en)	1994-06-08	Pyrrole thiocaroxamide insecticidal and acaricidal agents
US6242647B1 (en)	2001-06-05	Insecticidal biphenylthiohydrazides
US5362746A (en)	1994-11-08	Process for the manufacture of insecticidal 2-aryl-1-(alkoxymethyl)-4-halo-5-(trifluoromethyl)pyrroles
EP0487870A2 (en)	1992-06-03	Insecticidal and acaricidal diarylpyrrolecarbonitrile and diarylnitropyrrole compounds
JPH0686442B2 (ja)	1994-11-02	新規ヘテロ環式化合物
JP2707239B2 (ja)	1998-01-28	シアノアルキルーヘテロ環式化合物及び殺虫剤
JP4512928B2 (ja)	2010-07-28	Ｎ−チアジアゾリルシクロアルカンカルボン酸アミド類およびこれを有効成分とする殺虫、殺ダニ剤
JPH08507500A (ja)	1996-08-13	有害生物防除剤として有用なピリミジン誘導体
HU216062B (hu)	1999-04-28	Hatóanyagként N-(oxi- és tio-alkil-karbonil-oxi-metil)-pirrol-származékokat tartalmazó inszekticid és akaricid készítmények, eljárás a hatóanyagok előállítására és eljárás a készítmények alkalmazására
JPH07196653A (ja)	1995-08-01	新規ヘテロ環式化合物
CA2450118A1 (en)	2002-12-12	Insecticidal biphenylthiohydrazides
AU2001268195A1 (en)	2002-12-16	Insecticidal biphenylthiohydrazides